Anthraquinone dyestuff for wool



Patented Oct. 21, 1952 ANTHRAQUINONE DYESTUFF FOR WOOL David I. Randall, Easton, Pa., and Edgar E. Benfrew, Phillipsburg, N. J assignors to General Aniline .&Fil m.0orporation, New YorlcIN. Y., a

corporation of Delaware No Drawing. Application November 17, 1950,

. Serial No. 196,350

5: Claims. (01. 260-272) 1 This invention relates to new and valuable compounds, which are useful as dyestuffs for W001 and which have a bright greenish-blue shade.

The new compounds have the following general formula,

-soai ll x R Q W our-m z wherein R. is selected from the group consisting of hydrogen and a lower alkyl group and X is selected. from the class consisting ofv hydrogen,

halogen, hydroxy, lowerv alkyl, lowerv alkoxy,

carboxyl'icand sulfonic acid groups and wherein Z represents an alk-ylene radical necessary to complete a lactanrring. It will be understood thatthe hydrogen of'the sulfonic acid group in the above formula maybe replaced by sodium or other metal.

These dyestuffs are generally prepared by-the reaction of bromamine acid with suitable amines.

The amines .arepreferably. prepared'in accordance with copending application, Serial No. 136,166; filedDecember 30,1949. In general the amines are prepared by condensing a nitr0- benzene compoundwith a-lactam or the like in the presence of formaldehyde, followed by reductionof the condensation product to the: corre sponding amino derivative.

As representative of the nitrobenzene employed in the condensation reaction the following may be mentioned: m-chloronitrobenzene, o-chloronitrobenzene, p chloronitrobenzene, p nitrotoluene, 2,3-dichloro-l-nitrobenzene, 2-chlorop-nitrotoluene, 3-chloro-p-nitrotoluene, 2,3-dichloro-p-nitrotoluene, 2,5-dichloro-p-nitrotoluene, p nitro tert. amylbenzene, o nitrotolu ene, m-nitrotoluene, 2-nitro-m-Xylene, 4-nitrom-xylene, 4-nitro-o-xylene, 3-nitro-p-xylene, 4- nitro-p-xylene, p-nitroanisole, o-nitroanisole, pnitrophenetole, o-nitrophenetole, 5-chloro-2- nitroanisole, 2-chloro-4-nitrophenetole, 5-chloro- 2 nitrotoluene, 6 chloro 2 nitrotoluene, 6- chloro 3 nitrotoluene, 4,5 dichloro 2 nitrotoluene.

The lactam may be for example one of the following: 2 pyrollidone ('y butyro'lact'am); 5- methyl-2-pyrollidone ('y-valerolactam) 2-piperidone (e-valerolactam), l-a'za-Z-cyclooctanone (7 suberolactam) 3 methyl 2 piperidone, 4- methyl-Z-piperidone, 3,3-dimethyl-2-piperidone, 3-ethyl-2-piperidin, S-propyl-Z-piperidone, 3- propyl-Z-piperidone, 5,5-dimethyl-3-isopropyl-2- pyrrolidone, l-aza- Z-cycloheptanone (2-homopiperidone), .6-methyl z-piperidone', 5-methyl-2- piperidone, 4-, 5-, 6- and 'Y-methyl-l-aza-2-cycloheptanone, 4,7,7-trimethyl 1-aza 2=cyc1oheptanone, 5,7,7-trimethyl-1-aza-2-heptanone, 3,5,5- trimethyl-1-aza-2-heptanone, 4,6;6-trimethyl-laza-Z-cycloheptanone, 4-isopropyl-7-methyl-laza-2-cycloheptanone; 4-methyl-Wisopropyl-lazo-2-cycloheptanone, l-isopropyl 5,6-dimethyl- Z-piperidone and the like. I

The following example illustrates a preferred embodiment of the invention but it will be understood that variations and modifications may be made within the scopetof the claims.

Example In a suitably equipped vessel was charged 30.3

parts by weight sodium 1.-arnino-l-bromoa.nthra quinoneQ-sulfonate, 20:4 parts 1-(53-amino-2 methylbenzyl) -2-pyrrolidone, 106] parts sodium" carbonate, 42 parts sodium bicarbonate, 1".0 parts" ouprous chloride and 800.0 parts water; The: mixture "was stirredat C. for sixteen hours.

Then wasa'd ded 50.0 parts. sodiumchloride; The

mixture was allowed to cool, whereupon a precipitate settled. It was collected onafilter; The" product may be purified by the usual well-known The product after reaction with an acid yielded bright greenish-blue dyeings of excellent properties when dyedon wool. The compound has the formula:

(N) NE:

In the same manner. as in the above example bromamine acid may be reacted with other N- (aminobenzyl) lactams such as those obtainable: by the formaldehyde condensation of the nitrobenzyl compounds and lactams listed abov fol-- lowed by reduction to the corresponding amino 3. A new dyestufl of the formula, derivative. For example, the following com- O NH pounds may be prepared in this manner: II

NH, com

SO:H

CH: 6 H E 10 OHZ-N-cH-QH,

H-CH: J

C- Hz H 2 4. A new dyestufl of the formula, 0 0 NH: 0 NH, I

l SOsH SO:H

H n O Q CH 5 0 NH 2- i Q Q /CH"" CH2 CHzN CHz HPN\ /CH: COH -om g 0 5. A method for preparing a new dyestuff of This is a continuation in part of our applicathe formula. tion Serial No. 132,398 filed'December 10, 1949. W I NHz What we claim is: 1. A new dyestufi of the general formula, 503E C) NHg -so H 3 Nil-OCH: H (5Hz-N-C=O 0 NE x R CH2 /CH2 5 40 cm CHPN/ which comprises reacting sodium 1-amino-4- bromoanthraquinone 2 sulfonate with 1 (5 amino-Z-methylbenzyl) -2-py1'rolidone. I O DAVID I. RANDALL. wherein R, is selected from the group consist- EDGAR E- R FREW.

ing of hydrogen and a lower alkyl group and a: is selected from the class consisting of hy- REFERENCES CITED drogen, halogen, hydroxy lower alkyl, lower al- The following references are of record in the koxy, carboxylic and sulfonic acid groups and file of this patent: wherein Z represents an alkylene radical nec- UNITED STATES PATENTS essary to complete a lactam ring of not more Number Name Date than six members.

2. A dyestuff of the formula, 2506'025 Jenny at May 1950 0 NH; V FOREIGYN PATENTS I H Number Country Date SOaH 171,956 Germany Decl 1,1934

C52 2 C I 

1. A NEW DYESTUFF OF THE GENERAL FORMULA, 